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Papers by Gerald Pattenden

Research paper thumbnail of Synthetic studies towards phorboxazole A. A convergent synthesis of the C31C46 polyene oxane-hemiacetal side chain

Tetrahedron Letters, 1998

A convergent and stereoselective synthesis of the C31-C46 side chain unit in the marine natural p... more A convergent and stereoselective synthesis of the C31-C46 side chain unit in the marine natural product phorboxazole A, which accommodates five asymmetric centres, three carbon-to-carbon double bonds and an oxane-hemiacetal unit, is described.

Research paper thumbnail of Studies Towards Funiculosin (I). Synthesis of the Unique all-cis- Cyclopentanetetrol Moiety

Research paper thumbnail of Production of chrysanthemic acid and pyrethrins by tissue cultures of Chrysanthemum cinerariaefolium

Plant Cell Rep, 1985

Tissue cultures of C h r y s a n t h e m u m cinerariaefolium were established, and then used to ... more Tissue cultures of C h r y s a n t h e m u m cinerariaefolium were established, and then used to study the production of pyrethrin insecticides, and their precursor chrysanthemic acid.

Research paper thumbnail of Application of nuclear magnetic resonance spectroscopy in the stereochemical assignment of poly-Z-isomeric conjugated polyene isoprenoids

J Chem Soc Perkin Trans 1, 1983

Research paper thumbnail of Effects of ulapualide A and synthetic macrolide analogues on actin dynamics and gene regulation

Cellular and Molecular Life Sciences Cmls, Feb 5, 2007

Several marine macrolide toxins act as potent and specific actin-severing molecules. Recent eluci... more Several marine macrolide toxins act as potent and specific actin-severing molecules. Recent elucidation of their stereochemistries and modes of interaction with actin has allowed the syntheses of bioactive analogues. Here we used synthetic analogues in a structure-function analysis of ulapualide A, a trisoxazole-based macrolide. Ulapualide A harboured potent actin-depolymerising activity both in cells and in vitro. Its synthetic diastereoisomer was three orders of magnitude less active than the natural toxin and synthetic macrolide fragments lacked actin-capping/ severing activity altogether. Modulation of serum response factor (SRF)-dependent gene expression, as described for other actin-binding toxins, was also examined. Specific changes in response to ulapualide A were not observed, primarily due to its profound effects on cytoskeletal integrity and cell adhesion. Several synthetic fragments of ulapualide A also had no effect on SRF-dependent gene expression. However, inhibition was observed with a molecule corresponding to the extended aliphatic side chain of halichondramide, a structurally related macrolide. These findings indicate that side-chain derivatives of trisoxazole-based macrolides may serve to uncouple gene-regulatory events from actin dynamics.

Research paper thumbnail of Tandem cyclisations involving ?-ketenyl alkyl radicals. New syntheses of the natural triquinanes pentalenene and modhephene

Org Biomol Chem, 2005

ABSTRACT

Research paper thumbnail of ChemInform Abstract: Total Synthesis of Thiangazole, a Novel Naturally Occurring HIV-1 Inhibitor from Polyangium sp

Cheminform, 2010

ABSTRACT ChemInform is a weekly Abstracting Service, delivering concise information at a glance t... more ABSTRACT ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Research paper thumbnail of Synthetic studies towards halichondramides, and related novel tris-oxazole containing macrolides from marine organisms. A concise route to the keto-triol formyl enamine moiety

Tetrahedron Letters, May 26, 1992

... Milton J. Kiefel, John Maddock and Gerald Pattenden* Department of Chemistry, The University,... more ... Milton J. Kiefel, John Maddock and Gerald Pattenden* Department of Chemistry, The University, Nottingham N(r7 2RD Key Words: Halichondramide; tris ... 13 TD Penning, SW Djuric, RA Haack, V. J, Kalish, JM Miyashiro, BW Rowell and SS Yu, Synthetic Commun., 1990, 20, 307. ...

Research paper thumbnail of Vinylcyclopropylacyl Radicals: Intramolecular Ketene Additions leading to Concise Syntheses of Cyclohexenones

Research paper thumbnail of Cascade radical cyclisations with vinylcyclopropane electrophores

Tetrahedron Letters, May 19, 1997

ABSTRACT

Research paper thumbnail of Consecutive 6-endo trigonal cyclisations from polyene acyl radical intermediates leading to decalone and perhydrophenanthrone ring constructions

Journal of the Chemical Society, Perkin Transactions 1, 1996

ABSTRACT

Research paper thumbnail of Synthetic studies towards phorboxazole A. A concise stereoselective synthesis of the C20_C26 pentasubstituted oxane ring unit

Tetrahedron Lett, 1998

A stereoselective synthesis of the 2,6-cis oxane unit, accommodating five contiguous asymmetric c... more A stereoselective synthesis of the 2,6-cis oxane unit, accommodating five contiguous asymmetric centres, found in the novel marine natural product phorboxazole A 1, is described.A stereoselective synthesis of the 2,6-cis oxane unit, accommodating five contiguous asymmetric centres, found in the novel marine natural product phorboxazole A, is described.

Research paper thumbnail of A new approach to fused carbocycles. Intramolecular photocyclisations of 1,3-dione enol acetates

Journal of the Chemical Society, Chemical Communications, 1979

Szmmary Irradiation of the enol acetate (1) gave the tricyclic adduct (2) regioselectively and in... more Szmmary Irradiation of the enol acetate (1) gave the tricyclic adduct (2) regioselectively and in quantitative yield, whereas (12) led (93%) to a mixture (3: 2) of adducts (13) and (14), and the enol acetates (9) and (10)

Research paper thumbnail of One-stage double methylene transfer reactions from methylsulphinylmethanide to activated double bonds. Mimetic of in vivo C-ethylation

Journal of the Chemical Society Perkin Transactions 1, 1974

Research paper thumbnail of Natural polyene α-pyrones. Total synthesis of citreomontanin from Penicillium pedomontanum

Tetrahedron Letters, 1985

ABSTRACT

Research paper thumbnail of Total Synthesis of Oxazole-Based Virginiamycin Antibiotics: 14,15-Anhydropristinamycin IIB

Synthesis Stuttgart, 1998

Research paper thumbnail of ChemInform Abstract: Synthesis and Metal-Templated Assembly of Oxazole and Thiazole-Based Amino Acids. Total Synthesis of Nostocyclamide (Ia) and Related Cyclic Peptides

Research paper thumbnail of ChemInform Abstract: Total Synthesis and Assignment of Stereochemistry of Raocyclamide Cyclopeptides from Cyanobacterium Oscillatoria raoi

Cheminform, 2010

ABSTRACT ChemInform is a weekly Abstracting Service, delivering concise information at a glance t... more ABSTRACT ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Research paper thumbnail of An Attempted Cascade Radical-Mediated Cyclisation Approach to Ring-D Aromatic Steroids

Research paper thumbnail of A Macrolactamisation-Oxazoline Ring Forming Approach Towards the Tris-Oxazole Macrolide Core in the Ulapualides

Research paper thumbnail of Synthetic studies towards phorboxazole A. A convergent synthesis of the C31C46 polyene oxane-hemiacetal side chain

Tetrahedron Letters, 1998

A convergent and stereoselective synthesis of the C31-C46 side chain unit in the marine natural p... more A convergent and stereoselective synthesis of the C31-C46 side chain unit in the marine natural product phorboxazole A, which accommodates five asymmetric centres, three carbon-to-carbon double bonds and an oxane-hemiacetal unit, is described.

Research paper thumbnail of Studies Towards Funiculosin (I). Synthesis of the Unique all-cis- Cyclopentanetetrol Moiety

Research paper thumbnail of Production of chrysanthemic acid and pyrethrins by tissue cultures of Chrysanthemum cinerariaefolium

Plant Cell Rep, 1985

Tissue cultures of C h r y s a n t h e m u m cinerariaefolium were established, and then used to ... more Tissue cultures of C h r y s a n t h e m u m cinerariaefolium were established, and then used to study the production of pyrethrin insecticides, and their precursor chrysanthemic acid.

Research paper thumbnail of Application of nuclear magnetic resonance spectroscopy in the stereochemical assignment of poly-Z-isomeric conjugated polyene isoprenoids

J Chem Soc Perkin Trans 1, 1983

Research paper thumbnail of Effects of ulapualide A and synthetic macrolide analogues on actin dynamics and gene regulation

Cellular and Molecular Life Sciences Cmls, Feb 5, 2007

Several marine macrolide toxins act as potent and specific actin-severing molecules. Recent eluci... more Several marine macrolide toxins act as potent and specific actin-severing molecules. Recent elucidation of their stereochemistries and modes of interaction with actin has allowed the syntheses of bioactive analogues. Here we used synthetic analogues in a structure-function analysis of ulapualide A, a trisoxazole-based macrolide. Ulapualide A harboured potent actin-depolymerising activity both in cells and in vitro. Its synthetic diastereoisomer was three orders of magnitude less active than the natural toxin and synthetic macrolide fragments lacked actin-capping/ severing activity altogether. Modulation of serum response factor (SRF)-dependent gene expression, as described for other actin-binding toxins, was also examined. Specific changes in response to ulapualide A were not observed, primarily due to its profound effects on cytoskeletal integrity and cell adhesion. Several synthetic fragments of ulapualide A also had no effect on SRF-dependent gene expression. However, inhibition was observed with a molecule corresponding to the extended aliphatic side chain of halichondramide, a structurally related macrolide. These findings indicate that side-chain derivatives of trisoxazole-based macrolides may serve to uncouple gene-regulatory events from actin dynamics.

Research paper thumbnail of Tandem cyclisations involving ?-ketenyl alkyl radicals. New syntheses of the natural triquinanes pentalenene and modhephene

Org Biomol Chem, 2005

ABSTRACT

Research paper thumbnail of ChemInform Abstract: Total Synthesis of Thiangazole, a Novel Naturally Occurring HIV-1 Inhibitor from Polyangium sp

Cheminform, 2010

ABSTRACT ChemInform is a weekly Abstracting Service, delivering concise information at a glance t... more ABSTRACT ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Research paper thumbnail of Synthetic studies towards halichondramides, and related novel tris-oxazole containing macrolides from marine organisms. A concise route to the keto-triol formyl enamine moiety

Tetrahedron Letters, May 26, 1992

... Milton J. Kiefel, John Maddock and Gerald Pattenden* Department of Chemistry, The University,... more ... Milton J. Kiefel, John Maddock and Gerald Pattenden* Department of Chemistry, The University, Nottingham N(r7 2RD Key Words: Halichondramide; tris ... 13 TD Penning, SW Djuric, RA Haack, V. J, Kalish, JM Miyashiro, BW Rowell and SS Yu, Synthetic Commun., 1990, 20, 307. ...

Research paper thumbnail of Vinylcyclopropylacyl Radicals: Intramolecular Ketene Additions leading to Concise Syntheses of Cyclohexenones

Research paper thumbnail of Cascade radical cyclisations with vinylcyclopropane electrophores

Tetrahedron Letters, May 19, 1997

ABSTRACT

Research paper thumbnail of Consecutive 6-endo trigonal cyclisations from polyene acyl radical intermediates leading to decalone and perhydrophenanthrone ring constructions

Journal of the Chemical Society, Perkin Transactions 1, 1996

ABSTRACT

Research paper thumbnail of Synthetic studies towards phorboxazole A. A concise stereoselective synthesis of the C20_C26 pentasubstituted oxane ring unit

Tetrahedron Lett, 1998

A stereoselective synthesis of the 2,6-cis oxane unit, accommodating five contiguous asymmetric c... more A stereoselective synthesis of the 2,6-cis oxane unit, accommodating five contiguous asymmetric centres, found in the novel marine natural product phorboxazole A 1, is described.A stereoselective synthesis of the 2,6-cis oxane unit, accommodating five contiguous asymmetric centres, found in the novel marine natural product phorboxazole A, is described.

Research paper thumbnail of A new approach to fused carbocycles. Intramolecular photocyclisations of 1,3-dione enol acetates

Journal of the Chemical Society, Chemical Communications, 1979

Szmmary Irradiation of the enol acetate (1) gave the tricyclic adduct (2) regioselectively and in... more Szmmary Irradiation of the enol acetate (1) gave the tricyclic adduct (2) regioselectively and in quantitative yield, whereas (12) led (93%) to a mixture (3: 2) of adducts (13) and (14), and the enol acetates (9) and (10)

Research paper thumbnail of One-stage double methylene transfer reactions from methylsulphinylmethanide to activated double bonds. Mimetic of in vivo C-ethylation

Journal of the Chemical Society Perkin Transactions 1, 1974

Research paper thumbnail of Natural polyene α-pyrones. Total synthesis of citreomontanin from Penicillium pedomontanum

Tetrahedron Letters, 1985

ABSTRACT

Research paper thumbnail of Total Synthesis of Oxazole-Based Virginiamycin Antibiotics: 14,15-Anhydropristinamycin IIB

Synthesis Stuttgart, 1998

Research paper thumbnail of ChemInform Abstract: Synthesis and Metal-Templated Assembly of Oxazole and Thiazole-Based Amino Acids. Total Synthesis of Nostocyclamide (Ia) and Related Cyclic Peptides

Research paper thumbnail of ChemInform Abstract: Total Synthesis and Assignment of Stereochemistry of Raocyclamide Cyclopeptides from Cyanobacterium Oscillatoria raoi

Cheminform, 2010

ABSTRACT ChemInform is a weekly Abstracting Service, delivering concise information at a glance t... more ABSTRACT ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Research paper thumbnail of An Attempted Cascade Radical-Mediated Cyclisation Approach to Ring-D Aromatic Steroids

Research paper thumbnail of A Macrolactamisation-Oxazoline Ring Forming Approach Towards the Tris-Oxazole Macrolide Core in the Ulapualides